The proliferation of highly capable open-weight Small Language Models (SLMs) democratizes access to advanced cybersecurity capabilities, posing an escalating risk as these models can bypass proprietary API guardrails when deployed locally. However, SLMs deployed as autonomous agents often struggle with long-horizon, exploratory tasks like cybersecurity Capture The Flag (CTF) challenges due to context bloat and cognitive degradation from accumulated tool-call outputs. To understand and mitigate this cybersecurity threat, we introduce context segmentation, a two-level agentic framework that divides complex exploitation tasks into manageable, contextually isolated sub-problems. Evaluating on the picoCTF dataset using memory-constrained gemma-4 models, we demonstrate that for the E4B model, our strategy acts as an intelligent search, achieving competitive rewards with superior token efficiency compared to brute-force retries, and successfully solving 18.52% of tasks that standard agentic execution fails to complete. Code is available at https://github.com/9xeb/context-segmentation.
Large Language Model (LLM) agents are increasingly proposed to automate offensive security tasks, with recent studies reporting near human-level success rates in Capture-the-Flag (CTF) challenges. We here revisit these results, providing a second look at these claims. We engineer different agent architectures of increasing complexity and modularity on 30 web-based CTFs challenges spanning 14 vulnerability classes. We instantiate these agents with multiple LLM backbones, and compare them with claude-code, a general-purpose agent that automatically determines its internal architecture. Our evaluation yields three main findings. First, claude-code achieves performance comparable to the engineered architectures (19/30 solved tasks), suggesting that general-purpose agents are strong baselines for offensive security tasks. Second, both our architectures and claude-code struggle in the same challenge categories, revealing persistent barriers that keep current agents below human-level capability. Third, by leveraging our manually designed architectures we can systematically measure the impact of additional components, finding that structured orchestration of specialized roles outperforms monolithic designs, improving run-to-run consistency, and reducing execution costs.
Recent advances in Large Language Models (LLMs) have enabled agentic systems for complex, multi-step tasks; cybersecurity is emerging as a prominent application. To evaluate such agents, researchers widely adopt Capture The Flag (CTF) benchmarks. However, current CTF benchmarks reuse existing challenges, which exposes them to data contamination and potential cheating. Notably, we confirmed these issues in practice by integrating web search tools into an existing agent. To address these limitations, we present CTFusion, a streaming evaluation framework built on Live CTFs. To achieve this, CTFusion preserves per-agent independence under a single team account and reduces competition impact by forwarding only the first correct flag per challenge. Moreover, we implement CTFusion as a Model Context Protocol (MCP) server on the widely used CTFd platform, which offers broad applicability to diverse CTF events and agent types. Through experiments with three LLMs, two agents, and five Live CTFs, we demonstrate that existing CTF benchmarks can be unreliable in assessing LLM-based agents, while CTFusion can serve as a robust solution for evaluating cybersecurity agents. We release CTFusion as open source to foster future research in this area.
Large Language Model (LLM) agents are increasingly proposed for autonomous cybersecurity tasks, but their capabilities in realistic offensive settings remain poorly understood. We present DeepRed, an open-source benchmark for evaluating LLM-based agents on realistic Capture The Flag (CTF) challenges in isolated virtualized environments. DeepRed places an agent in a Kali attacker environment with terminal tools and optional web search, connected over a private network to a target challenge, and records full execution traces for analysis. To move beyond binary solved/unsolved outcomes, we introduce a partial-credit scoring method based on challenge-specific checkpoints derived from public writeups, together with an automated summarise-then-judge labelling pipeline for assigning checkpoint completion from logs. Using DeepRed, we benchmark ten commercially accessible LLMs on ten VM-based CTF challenges spanning different challenge categories. The results indicate that current agents remain limited: the best model achieves only 35% average checkpoint completion, performing strongest on common challenge types and weakest on tasks requiring non-standard discovery and longer-horizon adaptation.